Fungicide n-cycloalkyl-n-biphenylmethyl-carboxamide derivatives

ABSTRACT

The present invention relates to N-cycloalkyl-N-biphenylmethyl-carboxamide derivatives of formula (I) 
     
       
         
         
             
             
         
       
     
     wherein A, Z 1 , Z 2 , Z 3 , X, n, Y and m represent various substituents, their process of preparation, preparation intermediate compounds, their use as fungicide active agents, particularly in the form of fungicide compositions and methods for the control of phytopathogenic fungi, notably of plants, using these compounds or compositions.

The present invention relates toN-cycloalkyl-N-biphenylmethyl-carboxamide derivatives, their process ofpreparation, preparation intermediate compounds, their use as fungicideactive agents, particularly in the form of fungicide compositions andmethods for the control of phytopathogenic fungi, notably of plants,using these compounds or compositions.

In international patent application WO-2002/083647 certain fungicidaland insecticidal N-biphenylmethyl-carboxamide derivatives aregenerically embraced in a broad disclosure of numerous compounds of thefollowing formula:

wherein R¹ can represent C₁-C₅-alkyl, R² can represent C₁-C₅-alkyl orthe like, R³ can represent hydrogen or C₁-C₃-alkyl and X can representvarious substituents among which hydrogen, halogen or C₁-C₃-alkyl.However, this document does not claim compounds wherein the nitrogenatom of the carboxamide residue can be substituted by a cycloalkylgroup.

In international patent application WO-1994/05642 certain fungicidal andinsecticidal N-biphenylmethyl-carboxamide derivatives are genericallyembraced in a broad disclosure of numerous compounds of the followingformula:

wherein R₁, R₂, R₃ and R₄ can represent hydrogen, C₁-C₄-alkyl,C₃-C₇-cycloalkyl or the like, X can represent oxygen, Y can be a directbond and R₅ can represent a phenyl group. However, there is nodisclosure in this document of any compound including a non-fused5-membered heterocyclic carboxamide or a cycloalkyl linked to thenitrogen atom of the carboxamide residue.

In international patent application WO-2007/087906 certain fungicidalN-benzyl-carboxamide derivatives are generically embraced in a broaddisclosure of numerous compounds of the following formula:

wherein A represents a carbo-linked, unsaturated or partially saturated,5-membered heterocyclyl group, Z₁ represents C₃-C₇-cycloalkyl, Z₂ and Z₃can represent hydrogen, C₁-C₈-alkyl, C₃-C₇-cycloalkyl or the like, nrepresents at least 1 and X can represent various substituents. However,this document does not specifically disclose nor suggest selecting suchcompounds wherein X can be a phenyl group.

It is always of high-interest in agriculture to use novel pesticidecompounds in order to avoid or to control the development of resistantstrains to the active ingredients. It is also of high-interest to usenovel compounds being more active than those already known, with the aimof decreasing the amounts of active compound to be used, whilst at thesame time maintaining effectiveness at least equivalent to the alreadyknown compounds. We have now found a new family of compounds thatpossess the above mentioned effects or advantages.

Accordingly, the present invention providesN-cycloalkyl-N-biphenylmethyl-carboxamide derivatives of formula (I)

wherein

-   -   A represents a carbo-linked, unsaturated or partially saturated,        5-membered heterocyclyl group that can be substituted by up to        four groups R;    -   Z¹ represents a non-substituted C₃-C₇-cycloalkyl or a        C₃-C₇-cycloalkyl substituted by up to 10 atoms or groups that        can be the same or different and that can be selected in the        list consisting of halogen atoms; cyano; C₁-C₈-alkyl;        C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be        the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkylaminocarbonyl; or        di-C₁-C₈-alkylaminocarbonyl;    -   Z² and Z³, that can be the same or different, represent a        hydrogen atom; C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-alkynyl; cyano;        nitro; a halogen atom; C₁-C₈-alkoxy; C₂ C₈-alkenyloxy;        C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl; C₁-C₈-alkylsulphenyl; amino;        C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; C₁-C₈-alkoxycarbonyl;        C₁-C₈-alkylcarbamoyl; di-C₁-C₈-alkylcarbamoyl;        N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl; or    -   Z² and Z³ together with the carbon atom to that they are linked        can form a substituted or non substituted C₃-C₇-cycloalkyl;    -   X and Y independently represent a halogen atom; nitro; cyano;        isonitrile; hydroxyl; sulfanyl; amino; pentafluoro-λ⁶-sulfanyl;        C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen        atoms that can be the same or different; C₁-C₈-alkylamino;        di-C₁-C₈-alkylamino; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkoxy-C₁-C₈-alkoxy;        C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up        to 9 halogen atoms that can be the same or different;        C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen        atoms that can be the same or different; C₂-C₈-alkynyl;        C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can        be the same or different C₂-C₈-alkenyloxy;        C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms that        can be the same or different; C₂-C₈-alkynyloxy;        C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms that        can be the same or different; C₃-C₇-cycloalkyl;        C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-cycloalkyl-C₂-C₈-alkenyl;        C₃-C₇-cycloalkyl-C₂-C₈-alkynyl; C₃-C₇-halogenocycloalkyl        comprising up to 9 halogen atoms that can be the same or        different; C₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl;        C₁-C₈-alkyl-C₃-C₇-cycloalkyl; C₆-C₁₄-bicycloalkyl; formyl;        formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl;        carbamate; (hydroxyimino)-C₁-C₈-alkyl; C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylcarbamoyl;        di-C₁-C₈-alkylcarbamoyl; N—C₁-C₈-alkyloxycarbamoyl;        C₁-C₈-alkoxycarbamoyl; N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl;        C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up        to 9 halogen atoms that can be the same or different;        C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl;        C₁-C₈-alkylcarbonyloxy; C₁-C₈-halogenoalkylcarbonyloxy        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkylcarbonylamino;        C₁-C₈-halogenoalkylcarbonylamino comprising up to 9 halogen        atoms that can be the same or different;        C₁-C₈-alkylaminocarbonyloxy; di-C₁-C₈-alkylaminocarbonyloxy;        C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulphenyl;        C₁-C₈-halogenoalkylsulphenyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylsulphinyl;        C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylsulphonyl;        C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkoxyimino;        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl;        (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl;        (C₂-C₈-alkynyloxyimino)-C₁-C₈-alkyl;        (benzyloxyimino)-C₁-C₈-alkyl; tri(C₁-C₈-alkyl)silyl;        tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; benzyloxy that can be        substituted by up to 5 groups Q; benzylsulfanyl that can be        substituted by up to 5 groups Q; benzylamino that can be        substituted by up to 5 groups Q; aryl that can be substituted by        up to 5 groups Q; aryloxy that can be substituted by up to 5        groups Q; arylamino that can be substituted by up to 5 groups Q;        arylsulfanyl that can be substituted by up to 5 groups Q;        aryl-C₁-C₈-alkyl that can be substituted by up to 5 groups Q;        aryl-C₂-C₈-alkenyl that can be substituted by up to 5 groups Q;        aryl-C₂-C₈-alkynyl that can be substituted by up to 5 groups Q;        aryl-C₃-C₇-cycloalkyl that can be substituted by up to 5 groups        Q; pyridinyl that can be substituted by up to 4 groups Q and        pyridinyloxy that can be substituted by up to 4 groups Q; or two        substituents X together with the consecutive carbon atoms to        that they are linked can form a 5- or 6-membered, saturated,        carbo- or hetero-cycle comprising up to 3 heteroatoms fused with        the phenyl ring to that the two substituent X are linked, that        can be substituted by up to 4 groups Q that can be the same or        different; or        -   two substituents Y together with the consecutive carbon            atoms to that they are linked can form a 5- or 6-membered,            saturated, carbo- or hetero-cycle comprising up to 3            heteroatoms fused with the phenyl ring to that the two            substituent X are linked, that can be substituted by up to 4            groups Q that can be the same or different;    -   n represents 0, 1, 2, 3 or 4;    -   m represents 0, 1, 2, 3, 4 or 5;    -   R independently represents a hydrogen atom; halogen atom; cyano;        isonitrile; nitro; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl;        C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; tri(C₁-C₈-alkyl)silyl;        C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl comprising up        to 9 halogen atoms that can be the same or different;        C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen        atoms that can be the same or different; C₂-C₈-alkenyl;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl        comprising up to 9 halogen atoms that can be the same or        different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9        halogen atoms that can be the same or different; C₂        C₈-alkenyloxy; C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl;        C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₁-C₈-alkylsulphinyl;        C₁-C₈-alkylsulphonyl; C₁-C₈alkoxyimino;        (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; (benzyloxyimino)-C₁-C₈-alkyl;        aryloxy; benzyloxy; benzylsulfanyl; benzylamino; aryl;        halogenoaryloxy comprising up to 9 halogen atoms that can be the        same or different; C₁-C₈-alkylcarbonyl;        C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkoxycarbonyl;        C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms        that can be the same or different; C₁-C₈-alkylaminocarbonyl;        di-C₁-C₈-alkylaminocarbonyl;    -   Q independently represents a halogen atom; cyano; isonitrile;        nitro; C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-alkynyl; C₁-C₈-alkoxy;        C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkoxy-C₁-C₈-alkoxy;        C₁-C₈-alkylsulphanyl; C₁-C₈-halogenoalkyl comprising up to 9        halogen atoms that can be the same or different;        C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can        be the same or different; C₂-C₈-halogenoalkynyl comprising up to        9 halogen atoms that can be the same or different;        C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can        be the same or different; C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl        comprising up to 9 halogen atoms that can be the same or        different; tri(C₁-C₈)alkylsilyl and        tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl;        as well as salts, N-oxides, metallic complexes, metalloidic        complexes and optically active or geometric isomers thereof;        with the exclusion of        N-cyclopropyl-N-[(6-methoxybiphenyl-3-yl)methyl]isoxazole-5-carboxamide.

Any of the compounds according to the invention can exist in one or moreoptical or chiral isomer forms depending on the number of asymmetriccentres in the compound. The invention thus relates equally to all theoptical isomers and to their racemic or scalemic mixtures (the term“scalemic” denotes a mixture of enantiomers in different proportions)and to the mixtures of all the possible stereoisomers, in allproportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods that are known per se by the manordinary skilled in the art.

Any of the compounds according to the invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods that are known perse by the man ordinary skilled in the art.

For the compounds according to the invention, the following genericterms are generally used with the following meanings:

-   -   halogen means either one of fluorine, bromine, chlorine or        iodine;    -   heteroatom can be nitrogen, oxygen or sulfur;    -   any alkyl group, alkenyl group or alkynyl group can be straight        or branched;    -   the term aryl means phenyl or naphthyl    -   in the case of an amino group or the amino moiety of any other        amino-containing group, substituted by two substituents that can        be the same or different, the two substituents together with the        nitrogen to that they are attached can form a heterocyclyl        group, preferably a 5 to 7-membered heterocyclyl group, that can        be substituted and can contain other hetero atoms, for example        morpholino or piperidinyl.

Preferred compounds according to the invention are compounds of formula(I) wherein A is selected in the list consisting of:

-   -   a heterocycle of formula (A¹)

wherein:R¹ to R³ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A²)

wherein:R⁴ to R⁶ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A³)

wherein:R⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to9 halogen atoms that can be the same or different;R⁸ represents a hydrogen atom or a C₁-C₅-alkyl;

-   -   a heterocycle of formula (A⁴)

wherein:R⁹ to R¹¹ that can be the same or different represent a hydrogen atom; ahalogen atom; C₁-C₅-alkyl; amino; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogenatoms that can be the same or different;

-   -   a heterocycle of formula (A⁵)

wherein:R¹² and R¹³ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R¹⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different or C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁶)

wherein:R¹⁵ represents a hydrogen atom; a halogen atom; a cyano; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R¹⁶ and R¹⁸ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkoxycarbonyl; C₁-C₅-halogenoalkoxy comprising upto 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R¹⁷ represent a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A⁷)

wherein:R¹⁹ represents a hydrogen atom or a C₁-C₅-alkylR²⁰ to R²² that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁸)

wherein:R²³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R²⁴ represents a hydrogen atom or C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A⁹)

wherein:R²⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R²⁶ represents a hydrogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A¹⁰)

wherein:R²⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R²⁸ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; C₁-C₅-alkylamino ordi(C₁-C₅-alkyl)amino;

-   -   a heterocycle of formula (A¹¹)

wherein:R²⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R³⁰ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atomsthat can be the same or different; amino; C₁-C₅-alkylamino ordi(C₁-C₅-alkyl)amino;

-   -   a heterocycle of formula (A¹²)

wherein:R³¹ represents a hydrogen atom or a C₁-C₅-alkylR³² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R³³ represents a hydrogen atom; a halogen atom; a nitro; C₁-C₅-alkyl;C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms thatcan be the same or different or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A¹³)

wherein:R³⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C3-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R³⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano;C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;R³⁶ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A¹⁴)

wherein:R³⁷ and R³⁸ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different; C₁-C₅-alkoxy or aC₁-C₅-alkylsulphanyl;R³⁹ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A¹⁵)

wherein:to R⁴⁰ and R⁴¹ that can be the same or different represent a hydrogenatom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising upto 9 halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A¹⁶)

wherein:R⁴² and R⁴³ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different or amino;

-   -   a heterocycle of formula (A¹⁷)

wherein:R⁴⁴ and R⁴⁵ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;

-   -   a heterocycle of formula (A¹⁸)

wherein:R⁴⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;R⁴⁶ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different or C₁-C₅-alkylsulfanyl;

-   -   a heterocycle of formula (A¹⁹)

wherein:R⁴⁹ and R⁴⁸ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A²⁰)

wherein:R⁵⁰ and R⁵¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different;

-   -   a heterocycle of formula (A²¹)

wherein:R⁵² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different.

-   -   a heterocycle of formula (A²²)

wherein:R⁵³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl orC₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different.

-   -   a heterocycle of formula (A²³)

wherein:R⁵⁴ and R⁵⁶ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R⁵⁵ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁴)

wherein:R⁵⁷ and R⁵⁹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R⁵⁸ represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁵)

wherein:R⁶⁰ and R⁶¹ that can be the same or different represent a hydrogen atom;a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9halogen atoms that can be the same or different;R⁶² represents a hydrogen atom or C₁-C₅-alkyl;

-   -   a heterocycle of formula (A²⁶)

wherein:R⁶⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl;C₃-C₅-cycloalkyl C₁-C₅-halogenoalkyl comprising up to 9 halogen atomsthat can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy orC₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different;R⁶³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano;C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxycomprising up to 9 halogen atoms that can be the same or different;amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino;R⁶⁴ represents a hydrogen atom or C₁-C₅-alkyl.

More preferred compounds according to the invention are compounds offormula (I) wherein A is selected in the list consisting of A²; A⁶; A¹⁰and A¹³ as herein-defined.

Even more preferred compounds are compounds of formula (I) wherein Arepresents A¹³ wherein R³⁴ represents a C₁-C₅-alkyl, C₁-C₅-halogenoalkylcomprising up to 9 halogen atoms that can be the same or different; orC₁-C₅-alkoxy; R³⁵ represents a hydrogen atom or a halogen atom and R³⁶represents a C₁-C₅-alkyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Z¹ represents a C₃-C₇ cycloalkyl substituted by upto 10 groups or atoms that can be the same or different and that can beselected in the list consisting of halogen atoms; C₁-C₈-alkyl;C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to9 halogen atoms that can be the same or different; more preferably Z¹represents a non-substituted C₃-C₇-cycloalkyl; even more preferably Z¹represents cyclopropyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein X independently represents a halogen atom;C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkoxy orC₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different.

Other more preferred compounds according to the invention are compoundsof formula (I) wherein two consecutive substituents X together with thephenyl ring form a substituted or non substituted 1,3-benzodioxolyl;1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl;1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; or indolinyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein Y independently represents a halogen atom; cyano;C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms thatcan be the same or different; or (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl. Othermore preferred compounds according to the invention are compounds offormula (I) wherein two consecutive substituents Y together with thephenyl ring form a substituted or non substituted 1,3-benzodioxolyl;1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl;1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; or indolinyl.

Other preferred compounds according to the invention are compounds offormula (I) wherein R independently represents a hydrogen atom; halogenatom; cyano; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino;tri(C₁-C₈-alkyl)silyl; C₁-C₈-halogenoalkyl comprising up to 9 halogenatoms that can be the same or different; C₁-C₈-alkoxy;C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be thesame or different; C₁-C₈-alkylsulfanyl; amino, hydroxyl; nitro;C₁-C₈-alkoxycarbonyl; or C₂-C₈-alkynyloxy.

The above mentioned preferences with regard to the substituents of thecompounds according to the invention can be combined in various manners.These combinations of preferred features thus provide sub-classes ofcompounds according to the invention. Examples of such sub-classes ofpreferred compounds according to the invention can be combined:

-   -   preferred features of A with preferred features of Z¹, Z², Z³,        X, Y, n, m, R and Q;    -   preferred features of Z¹ with preferred features of A, Z², Z³,        X, Y, n, m, R and Q;    -   preferred features of Z² with preferred features of A, Z¹, Z³,        X, Y, n, m, R and Q;    -   preferred features of Z³ with preferred features of A, Z¹, Z²,        X, Y, n, m, R and Q;    -   preferred features of X with preferred features of A, Z¹, Z²,        Z³, Y, n, m, R and Q;    -   preferred features of Y with preferred features of A, Z¹, Z²,        Z³, X, n, m, R and Q;    -   preferred features of n with preferred features of A, Z¹, Z²,        Z³, X, Y, m, R and Q;    -   preferred features of m with preferred features of A, Z¹, Z²,        Z³, X, Y, n, R and Q;    -   preferred features of R with preferred features of A, Z¹, Z²,        Z³, X, Y, n m and Q;    -   preferred features of Q with preferred features of A, Z¹, Z²,        Z³, X, Y, n, m and R.

In these combinations of preferred features of the substituents of thecompounds according to the invention, the said preferred features canalso be selected among the more preferred features of each of A, Z¹, Z²,Z³, X, Y, n, m, R and Q so as to form most preferred subclasses ofcompounds according to the invention.

The present invention also relates to a process for the preparation ofcompounds of formula (I). Thus according to a further aspect of thepresent invention, there is provided a process P1 for the preparation ofa compound of formula (I) as illustrated by the following reactionscheme:

wherein

-   -   A, Z¹ to Z³, X, Y, n and m are as herein-defined;    -   U¹ represents a halogen atom or a leaving group.

In process P1 according to the invention, step 1 can be performed ifappropriate in the presence of a solvent and if appropriate in thepresence of an acid binder.

N-cycloalkyl-amine derivatives of formula (II) are known or can beprepared by known processes such as reductive amination of aldehyde orketone (Bioorganics and Medicinal Chemistry Letters, 2006, p 2014synthesis of compounds 7 and 8), or reduction of imines (Tetrahedron,2005, p 11689), or nucleophilic substitution of halogen, mesylate ortosylate (Journal of Medicinal Chemistry, 2002, p 3887 preparation ofintermediate for compound 28).

Carboxylic acid derivatives of formula (III) are known or can beprepared by known processes (WO-93/11117; EP-545 099; Nucleosides &Nucleotides, 1987, p 737-759, Bioorg. Med. Chem., 2002, p 2105-2108).

Suitable acid binders for carrying out process P1 according to theinvention are in each case all inorganic and organic bases that arecustomary for such reactions. Preference is given to using alkalineearth metal, alkali metal hydride, alkali metal hydroxides or alkalimetal alkoxides, such as sodium hydroxide, sodium hydride, calciumhydroxide, potassium hydroxide, potassium tert-butoxide or otherammonium hydroxide, alkali metal carbonates, such as cesium carbonate,sodium carbonate, potassium carbonate, potassium bicarbonate, sodiumbicarbonate, alkali metal or alkaline earth metal acetates, such assodium acetate, potassium acetate, calcium acetate and also tertiaryamines, such as trimethylamine, triethylamine, diisopropylethylamine,tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine,N,N-dimethylaminopyridine, diazabicyclooctane (DABCO),diazabicyclononene (DBN) or diazabicycloundecene (DBU).

It is also possible to work in the absence of an additional condensingagent or to employ an excess of the amine component, so that itsimultaneously acts as acid binder agent.

Suitable solvents for carrying out process P1 according to the inventionare in each case all customary inert organic solvents. Preference isgiven to using optionally halogenated aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichlorethane or trichlorethane; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, or sulphones, such assulpholane.

When carrying out process P1 according to the invention, the reactiontemperatures can independently be varied within a relatively wide range.Generally, processes according to the invention are carried out attemperatures between 0° C. and 160° C., preferably between 10° C. and120° C. A way to control the temperature for the processes according tothe invention is to use micro-wave technology.

Process P1 according to the invention is generally independently carriedout under atmospheric pressure. However, in each case, it is alsopossible to operate under elevated or reduced pressure.

When carrying out step 1 of process P1 according to the invention,generally 1 mol or other an excess of the acid derivative of formula(III) and from 1 to 3 mol of acid binder are employed per mole of amineof formula (II). It is also possible to employ the reaction componentsin other ratios.

Work-up is carried out by customary methods. Generally, the reactionmixture is treated with water and the organic phase is separated offand, after drying, concentrated under reduced pressure. If appropriate,the remaining residue can be freed by customary methods, such aschromatography or recrystallization, from any impurities that can stillbe present.

Thus according to a further aspect of the present invention, there isprovided a second process P2 for the preparation of a compound offormula (I) as illustrated by the following reaction scheme:

wherein

-   -   A, Z¹ to Z³, X, Y, n and m are as herein-defined;    -   U² represents a halogen atom such as chlorine, bromine or        iodine;    -   W represents a boron derivative such as a boronic acid, a        boronic ester or a potassium trifluoroborate.

Process P2 can be performed in the presence of a palladium catalyst andif appropriate in the presence of a phosphine ligand or a N-heterocycliccarbene ligand and in the presence of a base and if appropriate in thepresence of a solvent.

Compounds of formula (IV) can be prepared by known processes(WO-2007/087906) and the preparation of compounds of formula (V) is wellknown.

Process P2 according to the invention can be carried out in the presenceof a catalyst, such as a metal salt or complex. Suitable metalderivatives for this purpose are based on palladium. Suitable metalsalts or complexes for this purpose are palladium chloride, palladiumacetate, tetrakis(triphenylphosphine)palladium,bis(dibenzylideneacetone)palladium, bis(triphenyl phosphine)palladiumdichloride or 1,1′-bis(diphenylphosphino) ferrocenepalladium(II)chloride.

It is also possible to generate a palladium complex in the reactionmixture by separate addition to the reaction of a palladium salt and aligand or salt, such as triethylphosphine, tri-tert-butylphosphine,tricyclohexylphosphine, 2-(dicyclohexylphosphine)biphenyl,2-(di-tert-butylphosphine)biphenyl,2-(dicyclohexylphosphine)-2′-(N,N-dimethylamino)biphenyl,triphenyl-phosphine, tris-(o-tolyl)phosphine, sodium3-(diphenylphosphino)benzenesulphonate,tris-2-(methoxyphenyl)-phosphine,2,2′-bis(diphenylphosphine)-1,1′-binaphthyl,1,4-bis(diphenyl-phosphine)butane, 1,2-bis(diphenylphosphine)ethane,1,4-bis(dicyclohexylphosphine)butane,1,2-bis(dicyclohexylphosphine)ethane,2-(dicyclohexylphosphine)-2′-(N,N-dimethylamino)-biphenyl,1,1′-bis(diphenylphosphino)ferrocene,(R)-(+1-[(S)-2-diphenylphosphino)-ferrocenyl]ethyldicyclohexylphosphine,tris-(2,4-tert-butylphenyl)phosphite or1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

It is also advantageous to choose the appropriate catalyst and/or ligandfrom commercial catalogues such as “Metal Catalysts for OrganicSynthesis” by Strem Chemicals or “Phosphorous Ligands and Compounds” byStrem Chemicals.

Suitable bases for carrying out process P2 according to the inventioncan be inorganic and organic bases which are customary for suchreactions. Preference is given to using alkaline earth metal or alkalimetal hydroxides, such as sodium hydroxide, calcium hydroxide, potassiumhydroxide or other ammonium hydroxide derivatives; alkaline earth metal,alkali metal or ammonium fluorides such as potassium fluoride, cesiumfluoride or tetrabutylammonium fluoride; alkaline earth metal or alkalimetal carbonates, such as sodium carbonate, potassium carbonate,potassium bicarbonate, sodium bicarbonate or cesium carbonate; alkalimetal or alkaline earth metal acetates, such as sodium acetate,potassium acetate or calcium acetate; alkali metal alcoholates, such aspotassium ter-butoxide or sodium ter-butoxide; alkali metal phosphates,such as tri-potassium phosphate; and also tertiary amines, such astrimethylamine, triethylamine, tributylamine, N,N-dimethylaniline,pyridine, N-methylpiperidine, N,N-dimethyl-aminopyridine,diazabicyclooctane (DABCO), diazabicyclononene (DBN) ordiaza-bicycloundecene (DBU).

Suitable solvents for carrying out process P2 according to the inventioncan be customary inert organic solvents. Preference is given to usingoptionally halogen atomated aliphatic, alicyclic or aromatichydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane,methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene,dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride,dichlorethane or trichlorethane; ethers, such as diethyl ether,diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane,tetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole;nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile orbenzonitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate, sulphoxides, such as dimethyl sulphoxide, or sulphones, such assulpholane.

It can also be advantageous, to carry out process P2 according to theinvention, with a co-solvent such as water or an alcohol such asmethanol, ethanol, propanol, i-propanol or t-butanol.

When carrying out process P2 according to the invention, the reactiontemperatures can independently be varied within a relatively wide range.Generally, processes according to the invention are carried out attemperatures between 0° C. and 160° C., preferably between 10° C. and120° C. A way to control the temperature for the processes according tothe invention is to use micro-wave technology.

Process P2 according to the invention is generally independently carriedout under atmospheric pressure. However, in each case, it is alsopossible to operate under elevated or reduced pressure.

When carrying out step 2 of process P2 according to the invention, 1 molor an excess of the boron derivative of formula (V) and from 1 to 5 molof base and from 0.01 to 20 mol percent of a palladium complex can beemployed per mole of compound of formula (IV).

It is also possible to employ the reaction components in other ratios.

Work-up is carried out by customary methods. Generally, the reactionmixture is treated with water and the organic phase is separated offand, after drying, concentrated under reduced pressure. If appropriate,the remaining residue can be freed by customary methods, such aschromatography or recrystallization, from any impurities that can stillbe present.

Compounds according to the invention can be prepared according to theabove described processes. It will nevertheless be understood that, onthe basis of his general knowledge and of available publications, theskilled worker will be able to adapt these processes according to thespecifics of each of the compounds according to the invention that isdesired to be synthesized.

Still in a further aspect, the present invention relates to compounds offormula (II) useful as intermediate compounds or materials for theprocess of preparation according to the invention.

The present invention thus provides compounds of formula (II):

wherein Z², Z³, X, Y, n and m are as herein-defined with the exclusionof N-(biphenyl-4-ylmethyl)cyclopropanamine andN-[1-(biphenyl-4-yl)ethyl]cyclopropanamine.

In a further aspect, the present invention also relates to a fungicidecomposition comprising an effective and non-phytotoxic amount of anactive compound of formula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention that is sufficient to control ordestroy the fungi present or liable to appear on the crops and that doesnot entail any appreciable symptom of phytotoxicity for the said crops.Such an amount can vary within a wide range depending on the fungus tobe controlled, the type of crop, the climatic conditions and thecompounds included in the fungicide composition according to theinvention. This amount can be determined by systematic field trials,that are within the capabilities of a person skilled in the art.

Thus, according to the invention, there is provided a fungicidecomposition comprising, as an active ingredient, an effective amount ofa compound of formula (I) as herein defined and an agriculturallyacceptable support, carrier or filler.

According to the invention, the term “support” denotes a natural orsynthetic, organic or inorganic compound with that the active compoundof formula (I) is combined or associated to make it easier to apply,notably to the parts of the plant. This support is thus generally inertand should be agriculturally acceptable. The support can be a solid or aliquid. Examples of suitable supports include clays, natural orsynthetic silicates, silica, resins, waxes, solid fertilisers, water,alcohols, in particular butanol, organic solvents, mineral and plantoils and derivatives thereof. Mixtures of such supports can also beused.

The composition according to the invention can also comprise additionalcomponents. In particular, the composition can further comprise asurfactant. The surfactant can be an emulsifier, a dispersing agent or awetting agent of ionic or non-ionic type or a mixture of suchsurfactants. Mention can be made, for example, of polyacrylic acidsalts, lignosulphonic acid salts, phenolsulphonic ornaphthalenesulphonic acid salts, polycondensates of ethylene oxide withfatty alcohols or with fatty acids or with fatty amines, substitutedphenols (in particular alkylphenols or arylphenols), salts ofsulphosuccinic acid esters, taurine derivatives (in particular alkyltaurates), phosphoric esters of polyoxyethylated alcohols or phenols,fatty acid esters of polyols and derivatives of the above compoundscontaining sulphate, sulphonate and phosphate functions. The presence ofat least one surfactant is generally essential when the active compoundand/or the inert support are water-insoluble and when the vector agentfor the application is water. Preferably, surfactant content can becomprised from 5% to 40% by weight of the composition.

Optionally, additional components can also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active compoundscan be combined with any solid or liquid additive, that complies withthe usual formulation techniques.

In general, the composition according to the invention can contain from0.05 to 99% by weight of active compound, preferably 10 to 70% byweight.

Compositions according to the invention can be used in various formssuch as aerosol dispenser, capsule suspension, cold fogging concentrate,dustable powder, emulsifiable concentrate, emulsion oil in water,emulsion water in oil, encapsulated granule, fine granule, flowableconcentrate for seed treatment, gas (under pressure), gas generatingproduct, granule, hot fogging concentrate, macrogranule, microgranule,oil dispersible powder, oil miscible flowable concentrate, oil miscibleliquid, paste, plant rodlet, powder for dry seed treatment, seed coatedwith a pesticide, soluble concentrate, soluble powder, solution for seedtreatment, suspension concentrate (flowable concentrate), ultra lowvolume (ULV) liquid, ultra low volume (ULV) suspension, waterdispersible granules or tablets, water dispersible powder for slurrytreatment, water soluble granules or tablets, water soluble powder forseed treatment and wettable powder. These compositions include not onlycompositions that are ready to be applied to the plant or seed to betreated by means of a suitable device, such as a spraying or dustingdevice, but also concentrated commercial compositions that must bediluted before application to the crop.

The compounds according to the invention can also be mixed with one ormore insecticide, fungicide, bactericide, attractant, acaricide orpheromone active substance or other compounds with biological activity.The mixtures thus obtained have normally a broadened spectrum ofactivity. The mixtures with other fungicide compounds are particularlyadvantageous.

Examples of suitable fungicide mixing partners can be selected in thefollowing lists:

(1) Inhibitors of the nucleic acid synthesis, for example benalaxyl,benalaxyl-M, bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl,hymexazol, metalaxyl, metalaxyl-M, ofurace, oxadixyl and oxolinic acid.(2) Inhibitors of the mitosis and cell division, for example benomyl,carbendazim, chlorfenazole, diethofencarb, ethaboxam, fuberidazole,pencycuron, thiabendazole, thiophanate, thiophanate-methyl and zoxamide.(3) Inhibitors of the respiration, for example diflumetorim asCl-respiration inhibitor; bixafen, boscalid, carboxin, fenfuram,flutolanil, fluopyram, furametpyr, furmecyclox, isopyrazam (mixture ofsyn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate1RS,4SR,9SR), isopyrazam (syn epimeric racemate 1RS,4SR,9RS), isopyrazam(syn-epimeric enantiomer 1R,4S,9R), isopyrazam (syn-epimeric enantiomer1S,4R,9S), isopyrazam (anti-epimeric racemate 1 RS,4SR,9SR), isopyrazam(anti-epimeric enantiomer 1R,4S,9S), isopyrazam (anti-epimericenantiomer 1S,4R,9R), mepronil, oxycarboxin, penflufen, penthiopyrad,sedaxane, thifluzamide as CII-respiration inhibitor; amisulbrom,azoxystrobin, cyazofamid, dimoxystrobin, enestroburin, famoxadone,fenamidone, fluoxastrobin, kresoxim-methyl, metominostrobin,orysastrobin, picoxystrobin, pyraclostrobin, pyraoxystrobin,pyrametostrobin, pyribencarb, trifloxystrobin as CIII-respirationinhibitor.(4) Compounds capable to act as an uncoupler, like for examplebinapacryl, dinocap, fluazinam and meptyldinocap.(5) Inhibitors of the ATP production, for example fentin acetate, fentinchloride, fentin hydroxide, and silthiofam.(6) Inhibitors of the amino acid and/or protein biosynthesis, forexample andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim and pyrimethanil.(7) Inhibitors of the signal transduction, for example fenpiclonil,fludioxonil and quinoxyfen.(8) Inhibitors of the lipid and membrane synthesis, for examplebiphenyl, chlozolinate, edifenphos, etridiazole, iodocarb, iprobenfos,iprodione, isoprothiolane, procymidone, propamocarb, propamocarbhydrochloride, pyrazophos, tolclofos-methyl and vinclozolin.(9) Inhibitors of the ergosterol biosynthesis, for example aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol,pefurazoate, penconazole, piperalin, prochloraz, propiconazole,prothioconazole, pyributicarb, pyrifenox, quinconazole, simeconazole,spiroxamine, tebuconazole, terbinafine, tetraconazole, triadimefon,triadimenol, tridemorph, triflumizole, triforine, triticonazole,uniconazole, viniconazole and voriconazole.(10) Inhibitors of the cell wall synthesis, for example benthiavalicarb,dimethomorph, flumorph, iprovalicarb, mandipropamid, polyoxins,polyoxorim, prothiocarb, validamycin A, and valifenalate.(11) Inhibitors of the melanine biosynthesis, for example carpropamid,diclocymet, fenoxanil, phthalide, pyroquilon and tricyclazole.(12) Compounds capable to induce a host defence, like for exampleacibenzolar-5-methyl, probenazole, and tiadinil.(13) Compounds capable to have a multisite action, like for examplebordeaux mixture, captafol, captan, chlorothalonil, copper naphthenate,copper oxide, copper oxychloride, copper preparations such as copperhydroxide, copper sulphate, dichlofluanid, dithianon, dodine, dodinefree base, ferbam, fluorofolpet, folpet, guazatine, guazatine acetate,iminoctadine, iminoctadine albesilate, iminoctadine triacetate,mancopper, mancozeb, maneb, metiram, metiram zinc, oxine-copper,propamidine, propineb, sulphur and sulphur preparations includingcalcium polysulphide, thiram, tolylfluanid, zineb and ziram.(14) Further compounds like for example2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, ethyl(2Z)-3-amino-2-cyano-3-phenylprop-2-enoate,N-[2-(1,3-dimethylbutyl)phenyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-1-methyl-N-(3′,4′,5′-trifluorobiphenyl-2-yl)-1H-pyrazole-4-carboxamide,3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide,(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylethanamide,(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-en-2-ylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one,(2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene}amino)oxy]methyl}phenyl)ethanamide,(2E)-2-(methoxyimino)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}ethanamide,(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylethenyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylethanamide,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,N-ethyl-N-methyl-N′-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}imidoformamide,N′-{5-(difluoromethyl)-2-methyl-4-[3-(trimethylsilyl)propoxy]phenyl}-N-ethyl-N-methylimidoformamide,O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl}1H-imidazole-1-carbothioate,N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N²-(methylsulfonyl)valinamide,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,5-amino-1,3,4-thiadiazole-2-thiol, propamocarb-fosetyl,1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl1H-imidazole-1-carboxylate,1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide,2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one, 2-phenylphenol and salts,3-(difluoromethyl)-1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide,3,4,5-trichloropyridine-2,6-dicarbonitrile,3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine,4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine,quinolin-8-ol, quinolin-8-ol sulfate (2:1) (salt), tebufloquin,5-methyl-6-octyl-3,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,5-ethyl-6-octyl-3,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,ametoctradin, benthiazole, bethoxazin, capsimycin, carvone,chinomethionat, chloroneb, cufraneb, cyflufenamid, cymoxanil,cyprosulfamide, dazomet, debacarb, dichlorophen, diclomezine, dicloran,difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomate,ferimzone, flu metover, fluopicolide, fluoroimide, flusulfamide,flutianil, fosetyl-aluminium, fosetyl-calcium, fosetyl-sodium,hexachlorobenzene, irumamycin, isotianil, methasulfocarb, methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylate,methyl isothiocyanate, metrafenone,(5-chloro-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone,mildiomycin, tolnifanide,N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloropyridine-3-carboxamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodopyridine-3-carboxamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide,natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl,octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts,phenazine-1-carboxylic acid, phenothrin, phosphorous acid and its salts,propamocarb fosetylate, propanosine-sodium, proquinazid, pyrroInitrine,quintozene, S-prop-2-en-1-yl5-amino-2-(1-methylethyl)-4-(2-methylphenyl)-3-oxo-2,3-dihydro-1H-pyrazole-1-carbothioate,tecloftalam, tecnazene, triazoxide, trichlamide,5-chloro-N′-phenyl-N′-prop-2-yn-1-ylthiophene-2-sulfonohydrazide,zarilamid,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxamide,N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalen-1-yl)-1,3-thiazole-4-carboxamide,3-(difluoromethyl)-N-[4-fluoro-2-(1,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamideand pentyl{6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylidene]amino}oxy)methyl]pyridin-2-yl}carbamate.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound can also beparticularly advantageous. Examples of suitable bactericide mixingpartners can be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulphate and other copper preparations.

The compounds of formula (I) and the fungicide composition according tothe invention can be used to curatively or preventively control thephytopathogenic fungi of plants or crops.

Thus, according to a further aspect of the invention, there is provideda method for curatively or preventively controlling the phytopathogenicfungi of plants or crops characterised in that a compound of formula (I)or a fungicide composition according to the invention is applied to theseed, the plant or to the fruit of the plant or to the soil wherein theplant is growing or wherein it is desired to grow.

The method of treatment according to the invention can also be useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the invention can also be useful to treat theoverground parts of the plant such as trunks, stems or stalks, leaves,flowers and fruit of the concerned plant.

Among the plants that can be protected by the method according to theinvention, mention can be made of cotton; flax; vine; fruit or vegetablecrops such as Rosaceae sp. (for instance pip fruit such as apples andpears, but also stone fruit such as apricots, almonds and peaches), toRibesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp.,Fagaceae sp., Moraceae sp., Oleaceae sp., Actimidaceae sp., Lauraceaesp., Musaceae sp. (for instance banana trees and plantins), Rubiaceaesp., Theaceae sp., Sterculiceae sp., Rutaceae sp. (for instance lemonsoranges and grapefruit); Solanaceae sp. (for instance tomatoes),Liliaceae sp., Asteraceae sp. (for instance lettuces), Umbelliferae sp.,Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp., Papilionaceae sp.(for instance peas), Rosaceae sp. (for instance strawberries); majorcrops such as Graminae sp. (for instance maize, lawn or cereals such aswheat, rye, rice, barley and triticale), Asteraceae sp. (for instancesunflower), Cruciferae sp. (for instance colza), Fabacae sp. (forinstance peanuts), Papilionaceae sp. (for instance soybean), Solanaceaesp. (for instance potatoes), Chenopodiaceae sp. (for instancebeetroots), Elaeis sp. (for instance oil palm); horticultural and forestcrops; as well as genetically modified homologues of these crops.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants inwhich a heterologous gene has been stably integrated into the genome.The expression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, co suppression technology or RNAinterference—RNAi-technology). A heterologous gene that is located inthe genome is also called a transgene. A transgene that is defined byits particular location in the plant genome is called a transformationor transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the active compounds and compositions which can be usedaccording to the invention, better plant growth, increased tolerance tohigh or low temperatures, increased tolerance to drought or to water orsoil salt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, largerplant height, greener leaf color, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products are possible, which exceed theeffects which were actually to be expected.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect in plants.Accordingly, they are also suitable for mobilizing the defense system ofthe plant against attack by unwanted phytopathogenic fungi and/ormicroorganisms and/or viruses. This may, if appropriate, be one of thereasons of the enhanced activity of the combinations according to theinvention, for example against fungi. Plant-strengthening(resistance-inducing) substances are to be understood as meaning, in thepresent context, those substances or combinations of substances whichare capable of stimulating the defense system of plants in such a waythat, when subsequently inoculated with unwanted phytopathogenic fungiand/or microorganisms and/or viruses, the treated plants display asubstantial degree of resistance to these unwanted phytopathogenic fungiand/or microorganisms and/or viruses. In the present case, unwantedphytopathogenic fungi and/or microorganisms and/or viruses are to beunderstood as meaning phytopathogenic fungi, bacteria and viruses. Thus,the substances according to the invention can be employed for protectingplants against attack by the abovementioned pathogens within a certainperiod of time after the treatment. The period of time within whichprotection is effected generally extends from 1 to 10 days, preferably 1to 7 days, after the treatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozon exposure, highlight exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stress factors. Such plants are typicallymade by crossing an inbred male-sterile parent line (the female parent)with another inbred male-fertile parent line (the male parent). Hybridseed is typically harvested from the male sterile plants and sold togrowers. Male sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or males flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants is fully restored. This can be accomplished by ensuring that themale parents have appropriate fertility restorer genes which are capableof restoring the male fertility in hybrid plants that contain thegenetic determinants responsible for male-sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species (WO 1992/005251, WO 1995/009910, WO 1998/27806, WO2005/002324, WO 2006/021972 and U.S. Pat. No. 6,229,072). However,genetic determinants for male sterility can also be located in thenuclear genome. Male sterile plants can also be obtained by plantbiotechnology methods such as genetic engineering. A particularly usefulmeans of obtaining male-sterile plants is described in WO 1989/10396 inwhich, for example, a ribonuclease such as barnase is selectivelyexpressed in the tapetum cells in the stamens. Fertility can then berestored by expression in the tapetum cells of a ribonuclease inhibitorsuch as barstar (e.g. WO 1991/002069).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-tolerant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate through different means. Forexample, glyphosate-tolerant plants can be obtained by transforming theplant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphatesynthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutantCT7) of the bacterium Salmonella typhimurium (Comai et al., Science(1983), 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.(Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), thegenes encoding a Petunia EPSPS (Shah et al., Science (1986), 233,478-481), a Tomato EPSPS (Gasser et al., J. Biol. Chem. (1988), 263,4280-4289), or an Eleusine EPSPS (WO 2001/66704). It can also be amutated EPSPS as described in for example EP-A 0837944, WO 2000/066746,WO 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also beobtained by expressing a gene that encodes a glyphosate oxido-reductaseenzyme as described in U.S. Pat. No. 5,776,760 and U.S. Pat. No.5,463,175. Glyphosate-tolerant plants can also be obtained by expressinga gene that encodes a glyphosate acetyl transferase enzyme as describedin for example WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO2007/024782. Glyphosate-tolerant plants can also be obtained byselecting plants containing naturally-occurring mutations of theabove-mentioned genes, as described in for example WO 2001/024615 or WO2003/013226. Other herbicide resistant plants are for example plantsthat are made tolerant to herbicides inhibiting the enzyme glutaminesynthase, such as bialaphos, phosphinothricin or glufosinate. Suchplants can be obtained by expressing an enzyme detoxifying the herbicideor a mutant glutamine synthase enzyme that is resistant to inhibition.One such efficient detoxifying enzyme is an enzyme encoding aphosphinothricin acetyltransferase (such as the bar or pat protein fromStreptomyces species). Plants expressing an exogenous phosphinothricinacetyltransferase are for example described in U.S. Pat. No. 5,561,236;U.S. Pat. No. 5,648,477; U.S. Pat. No. 5,646,024; U.S. Pat. No.5,273,894; U.S. Pat. No. 5,637,489; U.S. Pat. No. 5,276,268; U.S. Pat.No. 5,739,082; U.S. Pat. No. 5,908,810 and U.S. Pat. No. 7,112,665.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase(HPPD). Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze thereaction in which para-hydroxyphenylpyruvate (HPP) is transformed intohomogentisate. Plants tolerant to HPPD-inhibitors can be transformedwith a gene encoding a naturally-occurring resistant HPPD enzyme, or agene encoding a mutated HPPD enzyme as described in WO 1996/038567, WO1999/024585 and WO 1999/024586. Tolerance to HPPD-inhibitors can also beobtained by transforming plants with genes encoding certain enzymesenabling the formation of homogentisate despite the inhibition of thenative HPPD enzyme by the HPPD-inhibitor. Such plants and genes aredescribed in WO 1999/034008 and WO 2002/36787. Tolerance of plants toHPPD inhibitors can also be improved by transforming plants with a geneencoding an enzyme prephenate dehydrogenase in addition to a geneencoding an HPPD-tolerant enzyme, as described in WO 2004/024928.

Still further herbicide resistant plants are plants that are madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pyrimidinyloxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides, as described for examplein Tranel and Wright, Weed Science (2002), 50, 700-712, but also, inU.S. Pat. No. 5,605,011, U.S. Pat. No. 5,378,824, U.S. Pat. No.5,141,870, and U.S. Pat. No. 5,013,659. The production ofsulfonylurea-tolerant plants and imidazolinone-tolerant plants isdescribed in U.S. Pat. No. 5,605,011; U.S. Pat. No. 5,013,659; U.S. Pat.No. 5,141,870; U.S. Pat. No. 5,767,361; U.S. Pat. No. 5,731,180; U.S.Pat. No. 5,304,732; U.S. Pat. No. 4,761,373; U.S. Pat. No. 5,331,107;U.S. Pat. No. 5,928,937; and U.S. Pat. No. 5,378,824; and internationalpublication WO 1996/033270. Other imidazolinone-tolerant plants are alsodescribed in for example WO 2004/040012, WO 2004/106529, WO 2005/020673,WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351, and WO2006/060634. Further sulfonylurea- and imidazolinone-tolerant plants arealso described in for example WO 2007/024782.

Other plants tolerant to imidazolinone and/or sulfonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding as described for examplefor soybeans in U.S. Pat. No. 5,084,082, for rice in WO 1997/41218, forsugar beet in U.S. Pat. No. 5,773,702 and WO 1999/057965, for lettuce inU.S. Pat. No. 5,198,599, or for sunflower in WO 2001/065922.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance. An “insect-resistanttransgenic plant”, as used herein, includes any plant containing atleast one transgene comprising a coding sequence encoding:

-   -   1) an insecticidal crystal protein from Bacillus thuringiensis        or an insecticidal portion thereof, such as the insecticidal        crystal proteins listed by Crickmore et al., Microbiology and        Molecular Biology Reviews (1998), 62, 807-813, updated by        Crickmore et al. (2005) at the Bacillus thuringiensis toxin        nomenclature, online at:        http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or        insecticidal portions thereof, e.g., proteins of the Cry protein        classes Cry1Ab, Cry1Ac, Cry1F, Cry2Ab, Cry3Aa, or Cry3Bb or        insecticidal portions thereof; or    -   2) a crystal protein from Bacillus thuringiensis or a portion        thereof which is insecticidal in the presence of a second other        crystal protein from Bacillus thuringiensis or a portion        thereof, such as the binary toxin made up of the Cry34 and Cry35        crystal proteins (Moellenbeck et al., Nat. Biotechnol. (2001),        19, 668-72; Schnepf et al., Applied Environm. Microbiol. (2006),        71, 1765-1774); or    -   3) a hybrid insecticidal protein comprising parts of different        insecticidal crystal proteins from Bacillus thuringiensis, such        as a hybrid of the proteins of 1) above or a hybrid of the        proteins of 2) above, e.g., the Cry1A.105 protein produced by        corn event MON98034 (WO 2007/027777); or    -   4) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation, such as the        Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A        protein in corn event MIR604;    -   5) an insecticidal secreted protein from Bacillus thuringiensis        or Bacillus cereus, or an insecticidal portion thereof, such as        the vegetative insecticidal (VIP) proteins listed at:        http://www.lifesci.sussex.ac.uk/home/Neil_Crickmore/Bt/vip.html,        e.g., proteins from the VIP3Aa protein class; or    -   6) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a second        secreted protein from Bacillus thuringiensis or B. cereus, such        as the binary toxin made up of the VIP1A and VIP2A proteins (WO        1994/21795); or    -   7) a hybrid insecticidal protein comprising parts from different        secreted proteins from Bacillus thuringiensis or Bacillus        cereus, such as a hybrid of the proteins in 1) above or a hybrid        of the proteins in 2) above; or    -   8) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation (while still        encoding an insecticidal protein), such as the VIP3Aa protein in        cotton event COT102.

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 8. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 8, to expand the range oftarget insect species affected when using different proteins directed atdifferent target insect species, or to delay insect resistancedevelopment to the plants by using different proteins insecticidal tothe same target insect species but having a different mode of action,such as binding to different receptor binding sites in the insect.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants include:

-   -   a. plants which contain a transgene capable of reducing the        expression and/or the activity of poly(ADP-ribose)polymerase        (PARP) gene in the plant cells or plants as described in WO        2000/004173 or WO2006/045633 or PCT/EP07/004,142.    -   b. plants which contain a stress tolerance enhancing transgene        capable of reducing the expression and/or the activity of the        PARG encoding genes of the plants or plants cells, as described        e.g. in WO 2004/090140.    -   c. plants which contain a stress tolerance enhancing transgene        coding for a plant-functional enzyme of the nicotinamide adenine        dinucleotide salvage synthesis pathway including nicotinamidase,        nicotinate phosphoribosyltransferase, nicotinic acid        mononucleotide adenyl transferase, nicotinamide adenine        dinucleotide synthetase or nicotine amide        phosphoribosyltransferase as described e.g. in WO2006/032469 or        WO 2006/133827 or PCT/EP07/002,433.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   -   1) transgenic plants which synthesize a modified starch, which        in its physical-chemical characteristics, in particular the        amylose content or the amylose/amylopectin ratio, the degree of        branching, the average chain length, the side chain        distribution, the viscosity behaviour, the gelling strength, the        starch grain size and/or the starch grain morphology, is changed        in comparison with the synthesised starch in wild type plant        cells or plants, so that this is better suited for special        applications. Said transgenic plants synthesizing a modified        starch are disclosed, for example, in EP 0571427, WO        1995/004826, EP 0719338, WO 1996/15248, WO 1996/19581, WO        1996/27674, WO 1997/11188, WO 1997/26362, WO 1997/32985, WO        1997/42328, WO 1997/44472, WO 1997/45545, WO 1998/27212, WO        1998/40503, WO99/58688, WO 1999/58690, WO 1999/58654, WO        2000/008184, WO 2000/008185, WO 2000/008175, WO 2000/28052, WO        2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO        2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO        2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO        2005/123927, WO 2006/018319, WO 2006/103107, WO 2006/108702, WO        2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO        2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP        07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO        2003/33540, WO 2004/078983, WO 2001/19975, WO 1995/26407, WO        1996/34968, WO 1998/20145, WO 1999/12950, WO 1999/66050, WO        1999/53072, U.S. Pat. No. 6,734,341, WO 2000/11192, WO        1998/22604, WO 1998/32326, WO 2001/98509, WO 2001/98509, WO        2005/002359, U.S. Pat. No. 5,824,790, U.S. Pat. No. 6,013,861,        WO 1994/004693, WO 1994/009144, WO 1994/11520, WO 1995/35026, WO        1997/20936.    -   2) transgenic plants which synthesize non starch carbohydrate        polymers or which synthesize non starch carbohydrate polymers        with altered properties in comparison to wild type plants        without genetic modification. Examples are plants producing        polyfructose, especially of the inulin and levan-type, as        disclosed in EP 0663956, WO 1996/001904, WO 1996/021023, WO        1998/039460, and WO 1999/024593, plants producing alpha 1,4        glucans as disclosed in WO 1995/031553, US 2002/031826, U.S.        Pat. No. 6,284,479, U.S. Pat. No. 5,712,107, WO 1997/047806, WO        1997/047807, WO 1997/047808 and WO 2000/014249, plants producing        alpha-1,6 branched alpha-1,4-glucans, as disclosed in WO        2000/73422, plants producing alternan, as disclosed in WO        2000/047727, EP 06077301.7, U.S. Pat. No. 5,908,975 and EP        0728213,    -   3) transgenic plants which produce hyaluronan, as for example        disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO        2007/039316, JP 2006/304779, and WO 2005/012529.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as cotton plants, with altered fibercharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants contain a mutation imparting such alteredfiber characteristics and include:

-   -   a) Plants, such as cotton plants, containing an altered form of        cellulose synthase genes as described in WO 1998/000549    -   b) Plants, such as cotton plants, containing an altered form of        rsw2 or rsw3 homologous nucleic acids as described in        WO2004/053219    -   c) Plants, such as cotton plants, with increased expression of        sucrose phosphate synthase as described in WO 2001/017333    -   d) Plants, such as cotton plants, with increased expression of        sucrose synthase as described in WO02/45485    -   e) Plants, such as cotton plants, wherein the timing of the        plasmodesmatal gating at the basis of the fiber cell is altered,        e.g. through downregulation of fiberselective β 1,3-glucanase as        described in WO2005/017157    -   f) Plants, such as cotton plants, having fibers with altered        reactivity, e.g. through the expression of        N-acteylglucosaminetransferase gene including nodC and        chitinsynthase genes as described in WO2006/136351

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation or by selection of plants contain amutation imparting such altered oil characteristics and include:

-   -   a) Plants, such as oilseed rape plants, producing oil having a        high oleic acid content as described e.g. in U.S. Pat. No.        5,969,169, U.S. Pat. No. 5,840,946 or U.S. Pat. No. 6,323,392 or        U.S. Pat. No. 6,063,947    -   b) Plants such as oilseed rape plants, producing oil having a        low linolenic acid content as described in U.S. Pat. No.        6,270,828, U.S. Pat. No. 6,169,190 or U.S. Pat. No. 5,965,755    -   c) Plant such as oilseed rape plants, producing oil having a low        level of saturated fatty acids as described e.g. in U.S. Pat.        No. 5,434,283

Particularly useful transgenic plants which may be treated according tothe invention are plants which comprise one or more genes which encodeone or more toxins, such as the following which are sold under the tradenames YIELD GARD® (for example maize, cotton, soya beans), KnockOut®(for example maize), BiteGard® (for example maize), Bt-Xtra® (forexample maize), StarLink® (for example maize), Bollgard® (cotton),Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example maize),Protecta® and NewLeaf® (potato). Examples of herbicide-tolerant plantswhich may be mentioned are maize varieties, cotton varieties and soyabean varieties which are sold under the trade names Roundup Ready®(tolerance to glyphosate, for example maize, cotton, soya bean), LibertyLink® (tolerance to phosphinotricin, for example oilseed rape), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentionedinclude the varieties sold under the name Clearfield® (for examplemaize).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, orcombination of transformation events, that are listed for example in thedatabases from various national or regional regulatory agencies (see forexample http://gmoinfo.jrc.it/gmp_browse.aspx andhttp://www.agbios.com/dbase.php).

The composition according to the invention may also be used againstfungal diseases liable to grow on or inside timber. The term “timber”means all types of species of wood, and all types of working of thiswood intended for construction, for example solid wood, high-densitywood, laminated wood, and plywood. The method for treating timberaccording to the invention mainly consists in contacting one or morecompounds according to the invention or a composition according to theinvention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

Among the diseases of plants or crops that can be controlled by themethod according to the invention, mention can be made of:

-   -   Powdery mildew diseases such as:    -   Blumeria diseases, caused for example by Blumeria graminis;    -   Podosphaera diseases, caused for example by Podosphaera        leucotricha;    -   Sphaerotheca diseases, caused for example by Sphaerotheca        fuliginea;    -   Uncinula diseases, caused for example by Uncinula necator;    -   Rust diseases such as:    -   Gymnosporangium diseases, caused for example by Gymnosporangium        sabinae;    -   Hemileia diseases, caused for example by Hemileia vastatrix;    -   Phakopsora diseases, caused for example by Phakopsora pachyrhizi        or Phakopsora meibomiae;    -   Puccinia diseases, caused for example by Puccinia recondite;    -   Uromyces diseases, caused for example by Uromyces        appendiculatus;    -   Oomycete diseases such as:    -   Albugo diseases caused for example by Albugo candida;    -   Bremia diseases, caused for example by Bremia lactucee;    -   Peronospora diseases, caused for example by Peronospora pisi        or P. brassicae;    -   Phytophthora diseases, caused for example by Phytophthora        infestans;    -   Plasmopara diseases, caused for example by Plasmopara viticola;    -   Pseudoperonospora diseases, caused for example by        Pseudoperonospora humuli or Pseudoperonospora cubensis;    -   Pythium diseases, caused for example by Pythium ultimum;    -   Leafspot, leaf blotch and leaf blight diseases such as:    -   Alternaria diseases, caused for example by Alternaria solani;    -   Cercospora diseases, caused for example by Cercospora beticola;    -   Cladiosporum diseases, caused for example by Cladiosporium        cucumerinum;    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus;    -   Colletotrichum diseases, caused for example by Colletotrichum        lindemuthanium;    -   Cycloconium diseases, caused for example by Cycloconium        oleaginum;    -   Diaporthe diseases, caused for example by Diaporthe citri;    -   Drechslera, Syn: Helminthosporium) or Cochliobolus miyabeanus;    -   Elsinoe diseases, caused for example by Elsinoe fawcettii;    -   Gloeosporium diseases, caused for example by Gloeosporium        laeticolor;    -   Glomerella diseases, caused for example by Glomerella cingulata;    -   Guignardia diseases, caused for example by Guignardia bidwelli;    -   Leptosphaeria diseases, caused for example by Leptosphaeria        maculans; Leptosphaeria nodorum;    -   Magnaporthe diseases, caused for example by Magnaporthe grisea;    -   Mycosphaerella diseases, caused for example by Mycosphaerella        graminicola;    -   Mycosphaerella arachidicola; Mycosphaerella fijiensis;    -   Phaeosphaeria diseases, caused for example by Phaeosphaeria        nodorum;    -   Pyrenophora diseases, caused for example by Pyrenophora teres;    -   Ramularia diseases, caused for example by Ramularia collo-cygni;    -   Rhynchosporium diseases, caused for example by Rhynchosporium        secalis;    -   Septoria diseases, caused for example by Septoria apii or        Septoria lycopercisi;    -   Typhula diseases, caused for example by Typhula incamata;    -   Venturia diseases, caused for example by Venturia inaequalis;    -   Root and stem diseases such as:    -   Corticium diseases, caused for example by Corticium graminearum;    -   Fusarium diseases, caused for example by Fusarium oxysporum;    -   Gaeumannomyces diseases, caused for example by Gaeumannomyces        graminis;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Sarocladium diseases caused for example by Sarocladium oryzae;    -   Sclerotium diseases caused for example by Sclerotium oryzae;    -   Tapesia diseases, caused for example by Tapesia acuformis;    -   Thielaviopsis diseases, caused for example by Thielaviopsis        basicola;    -   Ear and panicle diseases including maize cob, such as:    -   Alternaria diseases, caused for example by Alternaria spp.;    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Cladosporium diseases, caused for example by Cladosporium spp.;    -   Claviceps diseases, caused for example by Claviceps purpurea;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Monographella diseases, caused for example by Monographella        nivalis;    -   Smut and bunt diseases such as:    -   Sphacelotheca diseases, caused for example by Sphacelotheca        reiliana;    -   Tilletia diseases, caused for example by Tilletia caries;    -   Urocystis diseases, caused for example by Urocystis occulta;    -   Ustilago diseases, caused for example by Ustilago nuda;    -   Fruit rot and mould diseases such as:    -   Aspergillus diseases, caused for example by Aspergillus flavus;    -   Botrytis diseases, caused for example by Botrytis cinerea;    -   Penicillium diseases, caused for example by Penicillium        expansum;    -   Rhizopus diseases caused by example by Rhizopus stolonifer    -   Sclerotinia diseases, caused for example by Sclerotinia        sclerotiorum;    -   Verticilium diseases, caused for example by Verticilium        alboatrum;    -   Seed and soil borne decay, mould, wilt, rot and damping-off        diseases such as:    -   Alternaria diseases, caused for example by Alternaria        brassicicola    -   Aphanomyces diseases, caused for example by Aphanomyces        euteiches    -   Ascochyta diseases, caused for example by Ascochyta lentis    -   Aspergillus diseases, caused for example by Aspergillus flavus    -   Cladosporium diseases, caused for example by Cladosporium        herbarum    -   Cochliobolus diseases, caused for example by Cochliobolus        sativus    -   (Conidiaform: Drechslera, Bipolaris Syn: Helminthosporium);    -   Colletotrichum diseases, caused for example by Colletotrichum        coccodes;    -   Fusarium diseases, caused for example by Fusarium culmorum;    -   Gibberella diseases, caused for example by Gibberella zeae;    -   Macrophomina diseases, caused for example by Macrophomina        phaseolina    -   Monographella diseases, caused for example by Monographella        nivalis;    -   Penicillium diseases, caused for example by Penicillium expansum    -   Phoma diseases, caused for example by Phoma lingam    -   Phomopsis diseases, caused for example by Phomopsis sojae;    -   Phytophthora diseases, caused for example by Phytophthora        cactorum;    -   Pyrenophora diseases, caused for example by Pyrenophora graminea    -   Pyricularia diseases, caused for example by Pyricularia oryzae;    -   Pythium diseases, caused for example by Pythium ultimum;    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani;    -   Rhizopus diseases, caused for example by Rhizopus oryzae    -   Sclerotium diseases, caused for example by Sclerotium rolfsii;    -   Septoria diseases, caused for example by Septoria nodorum;    -   Typhula diseases, caused for example by Typhula incarnata;    -   Verticillium diseases, caused for example by Verticillium        dahliae;    -   Canker, broom and dieback diseases such as:    -   Nectria diseases, caused for example by Nectria gaffigena;    -   Blight diseases such as:    -   Monilinia diseases, caused for example by Monilinia taxa;    -   Leaf blister or leaf curl diseases such as:    -   Exobasidium diseases caused for nexample by Exobasidium vexans;    -   Taphrina diseases, caused for example by Taphrina deformans;    -   Decline diseases of wooden plants such as:    -   Esca diseases, caused for example by Phaemoniella clamydospora,        Phaeomoniella clamydospora, Phaeoacremonium aleophilum and        Fomitiporia mediterranea;    -   Eutypa dyeback, caused for example by Eutypa lata;    -   Dutch elm disease, caused for example by Ceratocystsc ulmi;    -   Ganoderma diseases caused by example by Ganoderma boninense;    -   Diseases of flowers and Seeds such as:    -   Botrytis diseases, caused for example by Botrytis cinerea;    -   Diseases of tubers such as:    -   Rhizoctonia diseases, caused for example by Rhizoctonia solani    -   Helminthosporium diseases, caused for example by        Helminthosporium solani.    -   Diseases of Tubers such as    -   Rhizoctonia diseases caused for example by Rhizoctonia solani;    -   Helminthosporium diseases caused for example by Helminthosporium        solani;    -   Club root diseases such as    -   Plasmodiophora diseases, caused for example by Plasmodiophora        brassicae;    -   Diseases caused by Bacterial Organisms such as    -   Xanthomanas species for example Xanthomonas campestris pv.        oryzae;    -   Pseudomonas species for example Pseudomonas syringae pv.        lachrymans;    -   Erwinia species for example Erwinia amylovora.

The fungicide composition according to the invention can also be usedagainst fungal diseases liable to grow on or inside timber. The term“timber” means all types of species of woodand all types of working ofthis wood intended for construction, for example solid wood,high-density wood, laminated wood and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds according to the invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active compound usually applied in the method of treatmentaccording to the invention is generally and advantageously from 10 to800 g/ha, preferably from 50 to 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously from 2 to 200 g per 100 kg of seed, preferably from 3 to150 g per 100 kg of seed in the case of seed treatment.

It is clearly understood that the doses indicated herein are given asillustrative examples of the method according to the invention. A personskilled in the art will know how to adapt the application doses, notablyaccording to the nature of the plant or crop to be treated.

The fungicide composition according to the invention can also be used inthe treatment of genetically modified organisms with the compoundsaccording to the invention or the agrochemical compositions according tothe invention. Genetically modified plants are plants into genome ofthat a heterologous gene encoding a protein of interest has been stablyintegrated. The expression “heterologous gene encoding a protein ofinterest” essentially means genes that give the transformed plant newagronomic properties, or genes for improving the agronomic quality ofthe modified plant.

The compounds or mixtures according to the invention can also be usedfor the preparation of composition useful to curatively or preventivelytreat human or animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The various aspects of the invention will now be illustrated withreference to the following table of compound examples and the followingpreparation or efficacy examples.

The following table illustrates in a non-limiting manner examples ofcompounds of formula (I) according to the invention.

In the following table, M+H (Apcl+) means the molecular ion peak plus 1a.m.u. (atomic mass unit) as observed in mass spectroscopy via positiveatmospheric pressure chemical ionisation.

In the following table, the logP values were determined in accordancewith EEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C18), using the methoddescribed below:

Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid andacetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (comprising 3to 16 carbon atoms) with known logP values (determination of the logPvalues by the retention times using linear interpolation between twosuccessive alkanones).

The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 190 nm to 400 nm.

In the following table, “position” denotes the point of attachment ofthe second phenyl ring on the first phenyl ring.

TABLE 1

      Example       A       Z²       Z³       (X)_(n)       position

logP     Mass (M + H)  1

Me H — 2-

378  2

H H — 2-

457  3

H H — 2-

400  4

H H — 3-

399  5

H H — 3-

364  6

H H — 3-

402  7

H H — 3-

400  8

H H — 3-

457  9

Me H — 4-

414 10

Me H — 4-

380 11

Me H — 4-

413 12

Me H — 4-

413 13

Me H — 4-

415 14

H H — 4-

432 15

H H 2-F 4-

450 16

H H 2-F 4-

3.8 17

H H — 4-

4.47 18

H H 2-F 4-

457 19

H H — 4-

398 20

H H — 4-

439 21

H H — 4-

416 22

H H — 4-

453 23

H H — 4-

453 24

H H — 4-

439 25

H H 2-F 4-

471 26

H H 2-F 4-

400 27

H H — 4-

382 28

H H — 4-

394 29

Me H — 4-

378 30

H H — 4-

3.01 31

H H 2-F 4-

457 32

H H 2-F 4-

434 33

H H 2-Cl 4-

398 34

Me H — 4-

432 35

H H — 4-

434 36

H H 2-F 4-

452 37

Me H — 4-

396 38

H H 2-Cl 4-

416 39

Me H — 4-

392 40

Me H — 4-

472 41

Me H — 4-

376 42

H H 2-Cl 5-

487 43

H H 2-Cl 5-

434

The following examples illustrate in a non-limiting manner thepreparation and efficacy of the compounds of formula (I) according tothe invention.

PREPARATION EXAMPLE 1N-[1-(biphenyl-2-yl)ethyl]-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide(compound 1)

To a solution of 300 mg (0.789 mmol) ofN-(2-bromobenzyl)-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamidein 10 ml of tetrahydrofurane are successively added 120 mg (0.986 mmol)of phenylboronic acid, 163 mg (1.183 mmol) of potassium carbonatedissolved in 5 ml of water and 9 mg (0.01 equivalent) oftetrakis(triphenylphosphine)palladium. The reaction mixture is heated at80° C. for 4 hrs. The reaction mixture is then cooled to ambienttemperature and poured on 50 ml of brine. The watery layer is extractedthree times with diethyl ether and the combined organic layers aresuccessively washed by a 1M solution of sodium hydroxide, brine andfiltered over a phase separator filter to yield after concentration 310mg of a brown oil. Column chromatography (gradient heptane/ethylacetate) yielded 220 mg (68% yield) ofN-[1-(biphenyl-2-yl)ethyl]-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideas a white solid; melting point [mp]=100° C.

PREPARATION EXAMPLE 2N-[(3-chlorobiphenyl-4-yl)methyl]-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide(compound 33) Step 1: preparation of 3-chlorobiphenyl-4-carbaldehyde

To a solution of 5 g (22.78 mmol) of 4-bromo-2-chlorobenzaldehyde in 30ml of tetrahydrofurane are successively added 3.47 g (28.47 mmol) ofphenylboronic acid, 4.72 g (34.17 mmol) of potassium carbonate dissolvedin 15 ml of water and 263 mg (0.01 equivalent) oftetrakis(triphenylphosphine) palladium. The reaction mixture is heatedat 80° C. for 3 hrs. The reaction mixture is then cooled to ambienttemperature and poured on 150 ml of brine. The watery layer is extractedthree times with dichloromethane and the combined organic layers aresuccessively washed by a 1M solution of sodium hydroxide, brine andfiltered over a ChemElut cartridge to yield after concentration 4.6 g ofa brown solid. Column chromatography (gradient heptane/chloroforme)yielded 3.29 g (65% yield) of 3-chlorobiphenyl-4-carbaldehyde as a whitesolid; mp=90-91° C.

Step 2: preparation of N-[(3-chlorobiphenyl-4-yl)methyl]cyclopropanamine

To a cooled solution of 1.82 ml (26 mmol) of cyclopropylamine and 1.90ml (33 mmol) of acetic acid, together with 3 g of 3 Å molecular sieves,in 45 ml of methanol, are added 2.85 g (13.1 mmol) of3-chlorobiphenyl-4-carbaldehyde. The reaction mixture is stirred for 4hrs at reflux. The reaction mixture is then cooled to ambienttemperature and 1.24 g (19.7 mmol) of sodium cyanoborohydride are slowlyadded. The reaction mixture is further stirred for 2 hrs at reflux. Thesolvent is removed under vacuum and 100 ml of water are then added tothe residue and the pH is adjusted to 10 with sodium hydroxyde. Thewatery layer is extracted three times with dichloromethane (3×50 ml);the combined organic layers are filtered over a phase separator filterto yield after concentration 11.61 g of a yellow oil. Columnchromatography (gradient heptane/ethyl acetate) yielded 2.84 g (79%yield) of N-[(3-chlorobiphenyl-4-yl)methyl]cyclopropanamine as acolourless oil (M+H=258).

Step 3: preparation ofN-[(3-chlorobiphenyl-4-yl)methyl]-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide

At ambient temperature, a solution of 226 mg (1.28 mmol) of5-fluoro-1,3-dimethyl-1H-pyrazole-4-carbonyl chloride in 1 ml oftetrahydrofurane is added dropwise to a solution of 300 mg (1.164 mmol)of N-[(3-chlorobiphenyl-4-yl)methyl]cyclopropanamine and 0.18 ml oftriethylamine in 5 ml tetrahydrofurane. The reaction mixture is stirredfor 15 hrs at room temperature. The solvent is removed under vacuum and10 ml of water are then added to the residue. The watery layer isextracted twice with ethyl acetate (2×50 ml) and the combined organiclayers are successively washed by a 1M solution of HCl, a saturatedsolution of potassium carbonate and brine and filtered over a ChemElutcartridge to yield after concentration 350 mg (72% yield) ofN-[(3-chlorobiphenyl-4-yl)methyl]-N-cyclopropyl-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamideas a yellow oil (M+H=398).

EXAMPLE A In Vivo Test on Alternaria brassicae (Leaf Spot of Crucifers)

The active ingredients tested are prepared by potter homogenization in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Radish plants (Pernot variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 18-20° C., are treated at thecotyledon stage by spraying with the active ingredient prepared asdescribed above.

Plants, used as controls, are treated with the mixture ofacetone/tween/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Alternaria brassicae spores (40,000 spores percm³). The spores are collected from a 12 to 13 days-old culture.

The contaminated radish plants are incubated for 6-7 days at about 18°C., under a humid atmosphere.

Grading is carried out 6 to 7 days after the contamination, incomparison with the control plants. Under these conditions, goodprotection (at least 70%) is observed at a dose of 500 ppm with thefollowing compounds: 3, 5, 7, 8, 11, 12, 15, 21, 25, 26, 27, 29, 31, 33,34, 38, 39, 42 and 43.

EXAMPLE B In Vivo Test on Pyrenophora teres (Barley Net Blotch)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Barley plants (Express variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the active ingredient prepared asdescribed above. Plants, used as controls, are treated with the mixtureof acetone/tween/DMSO/water not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Pyrenophora teres spores (12,000 spores per ml).The spores are collected from a 12-day-old culture. The contaminatedbarley plants are incubated for 24 hours at about 20° C. and at 100%relative humidity, and then for 12 days at 80% relative humidity.

Grading is carried out 12 days after the contamination, in comparisonwith the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: 1, 2, 4, 5,11, 12, 14, 15, 17, 19, 22, 23, 24, 25, 28, 29, 30, 31, 33, 34, 38, 39and 42.

EXAMPLE C In Vivo Test on Sphaerotheca fuliginea (Cucurbit PowderyMildew)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/water. This suspension is then diluted withwater to obtain the desired active material concentration.

Gherkin plants (Vert petit de Paris variety) in starter cups, sown on a50/50 peat soil-pozzolana substrate and grown at 20° C./23° C., aretreated at the 2 leaves stage by spraying with the aqueous suspensiondescribed above. Plants, used as controls, are treated with an aqueoussolution not containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Sphaerotheca fuliginea spores (100 000 spores perml). The spores are collected from a contaminated plants. Thecontaminated gherkin plants are incubated at about 20° C./25° C. and at60/70% relative humidity.

Grading (% of efficacy) is carried out 21 days after the contamination,in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: 1, 2, 3, 5,7, 8, 22, 25, 38, 39 and 42.

EXAMPLE D In Vivo Test on Mycosphaerella qraminicola (Wheat Leaf Spot)

The active ingredients tested are prepared by homogenization in amixture of acetone/tween/DMSO, then diluted with water to obtain thedesired active material concentration.

Wheat plants (Scipion variety), sown on a 50/50 peat soil-pozzolanasubstrate in starter cups and grown at 12° C., are treated at the 1-leafstage (10 cm tall) by spraying with the aqueous suspension describedabove. Plants, used as controls, are treated with an aqueous solutionnot containing the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Mycosphaerella graminicola spores (500 000 sporesper ml). The spores are collected from a 7-day-old culture. Thecontaminated wheat plants are incubated for 72 hours at 18° C. and at100% relative humidity, and then for 21 to 28 days at 90% relativehumidity.

Grading (% of efficacy) is carried out 21 to 28 days after thecontamination, in comparison with the control plants.

Under these conditions, good (at least 70%) or total protection isobserved at a dose of 500 ppm with the following compounds: 1, 2, 3, 4,5, 8, 9, 11, 14, 15, 17, 19, 20, 21, 22, 23, 24, 25, 28, 29, 30, 31, 32,34, 35, 36, 37, 39, 40, 41 and 42.

EXAMPLE E In Vivo Comparative Test on Peronospora parasitica (CruciferDowny Mildew)

Cabbage plants (Eminence variety) in starter cups, sown on a 50/50 peatsoil-pozzolana substrate and grown at 18-20° C., are treated at thecotyledon stage by spraying with the aqueous suspension described above.Plants, used as controls, are treated with an aqueous solution notcontaining the active material. After 24 hours, the plants arecontaminated by spraying them with an aqueous suspension of Peronosporaparasitica spores (50 000 spores per ml). The spores are collected frominfected plant. The contaminated cabbage plants are incubated for 5 daysat 20° C., under a humid atmosphere. Grading is carried out 5 days afterthe contamination, in comparison with the control plants.

Under these conditions, good (at least 70% of disease control) to totalprotection (100% of disease control) is observed at a dose of 500 ppmwith the following compounds: 7, 14 and 30 according to the inventionwhereas weak protection (less than 30% of disease control) to noprotection at all is observed at a dose of 500 ppm with the compounds ofexamples 358 and 489 disclosed in international patent applicationWO-2007/087906. Examples 358 and 489 disclosed in patent applicationWO-2007/087906 correspond, respectively, to following compounds:

-   N-cyclopropyl-N-[4-(2,4-dichlorophenoxy)benzyl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide;-   N-[4-(4-chlorophenoxy)benzyl]-N-cyclopropyl-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide.

These results show that the compounds according to the invention have amuch better biological activity than the structurally closest compoundsdisclosed in WO-2007/087906.

1. A compound of formula (I)

wherein A represents a carbo-linked, unsaturated or partially saturated, 5-membered heterocyclyl group that can be substituted by up to four groups R; Z¹ represents a non-substituted C₃-C₇-cycloalkyl or a C₃-C₇-cycloalkyl substituted by up to 10 atoms or groups that can be the same or different and that can be selected in the list consisting of halogen atoms; cyano; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl; Z² and Z³, that can be the same or different, represent a hydrogen atom; C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-alkynyl; cyano; nitro; a halogen atom; C₁-C₈-alkoxy; C₂ C₈-alkenyloxy; C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl; C₁-C₈-alkylsulphenyl; amino; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; C₁-C₈-alkoxycarbonyl; C₁-C₈-alkylcarbamoyl; di-C₁-C₈-alkylcarbamoyl; N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl; or Z² and Z³ together with the carbon atom to that they are linked can form a substituted or non substituted C₃-C₇-cycloalkyl; X and Y independently represent a halogen atom; nitro; cyano; isonitrile; hydroxyl; sulfanyl; amino; pentafluoro-λ⁶-sulfanyl; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈alkoxy-C₁-C₈-alkyl; C₁-C₈-alkoxy-C₁-C₈alkoxy; C₁-C₈alkylsulphanyl; C₁-C₈-halogenoalkylsulphanyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different C₂-C₈-alkenyloxy; C₂-C₈-halogenoalkenyloxy comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyloxy; C₂-C₈-halogenoalkynyloxy comprising up to 9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₃-C₇-cycloalkyl-C₂-C₈-alkenyl C₃-C₇-cycloalkyl-C₂-C₈-alkynyl; C₃-C₇-halogenocycloalkyl comprising up to 9 halogen atoms that can be the same or different; C₃-C₇-cycloalkyl-C₃-C₇-cycloalkyl; C₁-C₈-alkyl-C₃-C₇-cycloalkyl; C₆-C₁₄-bicycloalkyl; formyl; formyloxy; formylamino; carboxy; carbamoyl; N-hydroxycarbamoyl; carbamate; (hydroxyimino)-C₁-C₈-alkyl; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbamoyl; di-C₁-C₈-alkylcarbamoyl; N—C₁-C₈-alkyloxycarbamoyl; C₁-C₈-alkoxycarbamoyl; N—C₁-C₈-alkyl-C₁-C₈alkoxycarbamoyl; C₁-C₈-alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl; C₁-C₈-alkylcarbonyloxy; C₁-C₈-halogenoalkylcarbonyloxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbonylamino; C₁-C₈-halogenoalkylcarbonylamino comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyloxy; di-C₁-C₈-alkylaminocarbonyloxy; C₁-C₈-alkyloxycarbonyloxy, C₁-C₈-alkylsulphenyl; C₁-C₈-halogenoalkylsulphenyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphinyl; C₁-C₈-halogenoalkylsulphinyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulphonyl; C₁-C₈-halogenoalkylsulphonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxyimino; (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; (C₂-C₈-alkenyloxyimino)-C₁-C₈-alkyl; (C₂-C₈alkynyloxyimino)-C₁-C₈-alkyl; (benzyloxyimino)-C₁-C₈alkyl; tri(C₁-C₈-alkyl)silyl; tri(C₁-C₈-alkyl)silyl-C₁-C₈-alkyl; benzyloxy that can be substituted by up to 5 groups Q; benzylsulfanyl that can be substituted by up to 5 groups Q; benzylamino that can be substituted by up to 5 groups Q; aryl that can be substituted by up to 5 groups Q; aryloxy that can be substituted by up to 5 groups Q; arylamino that can be substituted by up to 5 groups Q; arylsulfanyl that can be substituted by up to 5 groups Q; aryl-C₁-C₈-alkyl that can be substituted by up to 5 groups Q; aryl-C₂-C₈-alkenyl that can be substituted by up to 5 groups Q; aryl-C₂-C₈-alkynyl that can be substituted by up to 5 groups Q; aryl-C₃-C₇-cycloalkyl that can be substituted by up to 5 groups Q; pyridinyl that can be substituted by up to 4 groups Q and pyridinyloxy that can be substituted by up to 4 groups Q; or two substituents X together with the consecutive carbon atoms to that they are linked can form a 5- or 6-membered, saturated, carbo- or hetero-cycle comprising up to 3 heteroatoms fused with the phenyl ring to that the two substituent X are linked, that can be substituted by up to 4 groups Q that can be the same or different; or two substituents Y together with the consecutive carbon atoms to that they are linked can form a 5- or 6-membered, saturated, carbo- or hetero-cycle comprising up to 3 heteroatoms fused with the phenyl ring to that the two substituent X are linked, that can be substituted by up to 4 groups Q that can be the same or different; n represents 0, 1, 2, 3 or 4; m represents 0, 1, 2, 3, 4 or 5; R independently represents a hydrogen atom; halogen atom; cyano; isonitrile; nitro; amino; sulfanyl; pentafluoro-λ⁶-sulfanyl; C₁-C₈-alkylamino; di-C₁-C₈alkylamino; tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkylsulfanyl; C₁-C₈-halogenoalkylsulfanyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkenyl; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-alkynyl; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₂ C₈alkenyloxy; C₂-C₈-alkynyloxy; C₃-C₇-cycloalkyl; C₃-C₇-cycloalkyl-C₁-C₈-alkyl; C₁-C₈-alkylsulphinyl; C₁-C₈alkylsulphonyl; C₁-C₈alkoxyimino; (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl; (benzyloxyimino)-C₁-C₈-alkyl; aryloxy; benzyloxy; benzylsulfanyl; benzylamino; aryl; halogenoaryloxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylcarbonyl; C₁-C₈-halogenoalkylcarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈alkoxycarbonyl; C₁-C₈-halogenoalkoxycarbonyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylaminocarbonyl; di-C₁-C₈-alkylaminocarbonyl; Q independently represents a halogen atom; cyano; isonitrile; nitro; C₁-C₈-alkyl; C₂-C₈-alkenyl; C₂-C₈-alkynyl; C₁-C₈-alkoxy; C₁-C₈-alkoxy-C₁-C₈-alkyl; C₁-C₈-alkoxy-C₁-C₈-alkoxy; C₁-C₈-alkylsulphanyl; C₁-C₈halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-halogenoalkenyl comprising up to 9 halogen atoms that can be the same or different; C₂-C₈-halogenoalkynyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-halogenoalkoxy-C₁-C₈-alkyl comprising up to 9 halogen atoms that can be the same or different; tri(C₁-C₈)alkylsilyl and tri(C₁-C₈)alkylsilyl-C₁-C₈-alkyl; as well as salts, N-oxides, metallic complexes, metalloidic complexes and optically active or geometric isomers thereof; with the exclusion of N-cyclopropyl-N-[(6-methoxybiphenyl-3-yl)methyl]isoxazole-5-carboxamide.
 2. A compound according to claim 1 wherein A is selected in the list consisting of: a heterocycle of formula (A¹)

wherein: R¹ to R³ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A²)

wherein: R⁴ to R⁶ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A³)

wherein: R⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R⁸ represents a hydrogen atom or a C₁-C₅-alkyl; a heterocycle of formula (A⁴)

wherein: R⁹ to R¹¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; amino; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁵)

wherein: R¹² and R¹³ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R¹⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; amino; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁶)

wherein: R¹⁵ represents a hydrogen atom; a halogen atom; a cyano; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R¹⁶ and R¹⁸ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkoxycarbonyl; C₁-C₅-alkyl; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R¹⁷ represent a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A⁷)

wherein: R¹⁹ represents a hydrogen atom or a C₁-C₅-alkyl R²⁰ to R²² that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁸)

wherein: R²³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R²⁴ represents a hydrogen atom or C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A⁹)

wherein: R²⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R²⁶ represents a hydrogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A¹⁰)

wherein: R²⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R²⁸ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino; a heterocycle of formula (A¹¹)

wherein: R²⁹ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R³⁰ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino; a heterocycle of formula (A¹²)

wherein: R³¹ represents a hydrogen atom or a C₁-C₅-alkyl R³² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R³³ represents a hydrogen atom; a halogen atom; a nitro; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A¹³)

wherein: R³⁴ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C3-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R³⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; C₁-C₅-alkylamino or di(C₁-C₅-alkylamino; R³⁶ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A¹⁴)

wherein: R³⁷ and R³⁸ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy or a C₁-C₅-alkylsulphanyl; R³⁹ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A¹⁵)

wherein: R⁴⁰ and R⁴¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A¹⁶)

wherein: R⁴² and R⁴³ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or amino; a heterocycle of formula (A¹⁷)

wherein: R⁴⁴ and R⁴⁵ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A¹⁸)

wherein: R⁴⁷ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R⁴⁶ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-alkylsulfanyl; a heterocycle of formula (A¹⁹)

wherein: R⁴⁹ and R⁴⁸ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A²⁰)

wherein: R⁵⁰ and R⁵¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₁-C₅-alkoxy; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; a heterocycle of formula (A²¹)

wherein: R⁵² represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different. a heterocycle of formula (A²²)

wherein: R⁵³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different. a heterocycle of formula (A²³)

wherein: R⁵⁴ and R⁵⁶ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R⁵⁵ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A²⁴)

wherein: R⁵⁷ and R⁵⁹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R⁵⁸ represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A²⁵)

wherein: R⁶⁰ and R⁶¹ that can be the same or different represent a hydrogen atom; a halogen atom; C₁-C₅-alkyl or C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; R⁶² represents a hydrogen atom or C₁-C₅-alkyl; a heterocycle of formula (A²⁶)

wherein: R⁶⁵ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; C₃-C₅-cycloalkyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-alkoxy; C₂-C₅-alkynyloxy or C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; R⁶³ represents a hydrogen atom; a halogen atom; C₁-C₅-alkyl; a cyano; C₁-C₅-alkoxy; C₁-C₅-alkylsulphanyl; C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₅-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; amino; C₁-C₅-alkylamino or di(C₁-C₅-alkyl)amino; R⁶⁴ represents a hydrogen atom or C₁-C₅-alkyl.
 3. A compound according to claim 2 wherein A is selected in the list consisting of A²; A⁶; A¹⁰ and A¹³.
 4. A compound according to claim 3 wherein A represents A¹³ wherein R³⁴ represents a C₁-C₅-alkyl, C₁-C₅-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different, or C₁-C₅-alkoxy; R³⁵ represents a hydrogen atom or a halogen atom; R³⁶ represents a C₁-C₅-alkyl.
 5. A compound according to claim 1 wherein Z¹ represents a C₃-C₇ cycloalkyl substituted by up to 10 groups or atoms that can be the same or different and that can be selected in the list consisting of halogen atoms; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.
 6. A compound according to claim 5 wherein Z¹ represents a non-substituted C₃-C₇-cycloalkyl.
 7. A compound according to claim 6 wherein Z¹ represents cyclopropyl.
 8. A compound according to claim 1 wherein X independently represents a halogen atom; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkoxy or C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different.
 9. A compound according to claim 1 wherein two consecutive substituents X together with the phenyl ring form a substituted or non substituted 1,3-benzodioxolyl; 1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl; 1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; or indolinyl.
 10. A compound according to claim 1 wherein Y independently represents a halogen atom; cyano; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; or (C₁-C₈-alkoxyimino)-C₁-C₈-alkyl.
 11. A compound according to claim 1 wherein two consecutive substituents Y together with the phenyl ring form a substituted or non substituted 1,3-benzodioxolyl; 1,2,3,4-tetrahydro-quinoxalinyl; 3,4-dihydro-2H-1,4-benzoxazinyl; 1,4-benzodioxanyl; indanyl; 2,3-dihydrobenzofuranyl; or indolinyl.
 12. A compound according to claim 1 wherein R independently represents a hydrogen atom; halogen atom; cyano; C₁-C₈-alkylamino; di-C₁-C₈-alkylamino; tri(C₁-C₈-alkyl)silyl; C₁-C₈-alkyl; C₁-C₈-halogenoalkyl comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkoxy; C₁-C₈-halogenoalkoxy comprising up to 9 halogen atoms that can be the same or different; C₁-C₈-alkylsulfanyl; amino, hydroxyl; nitro; C₁-C₈-alkoxycarbonyl; or C₂-C₈-alkynyloxy.
 13. A compound of formula (II)

wherein Z², Z³, X, Y, n and m are defined according to claim 1 with the exclusion of N-(biphenyl-4-ylmethyl)cyclopropanamine and N-[1-(biphenyl-4-yl)ethyl]cyclopropanamine.
 14. A fungicide composition comprising, as an active ingredient, an effective amount of a compound of formula (I) according to claim 1 and an agriculturally acceptable support, carrier or filler.
 15. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a compound according to claim 1 is applied to the soil where plants grow or are capable of growing, to the leaves or the fruit of plants or to the seeds of plants.
 16. A method for controlling phytopathogenic fungi of crops, characterized in that an agronomically effective and substantially non-phytotoxic quantity of a composition according to claim 14 is applied to the soil where plants grow or are capable of growing, to the leaves or the fruit of plants or to the seeds of plants. 